Sift just turned 15. To everyone who’s helped - thank you. We’ve protected thousands of businesses from billions of dollars of fraud, created 500+ jobs, and sold hundreds of millions of dollars of products and services.
I was 25 when we started the company. Fifteen years later, a few lessons stand above the rest. Here’s what I’d share with my younger self.
Lesson 1: Do the work that doesn’t look like work.
Despite your wildest career dreams coming true, you’ll feel empty inside, devoid of the passion, joy, and clarity you once had. For most of your life you’ve dismissed mental health, therapy or rest as optional luxuries for “soft” people. Founder CEOs aren’t soft. Just “be stronger.” Six years in, life loses its color. After the umpteenth consecutive weekend hiding from the world, lying in bed all day and stress eating your unfelt emotions, you’ll start wondering… This doesn’t seem normal. Am I depressed? What is depression? You’ll wear a brave smiling mask Monday to Friday while feeling lost and hopeless for another six years. What’s the point of life? Why do I exist? The burnout doesn’t help.
Looking back, you’ll see so clearly that everything was happening for you, not to you. Because you avoid conflict, intense conflict will find you. Because you struggle to feel your feelings, your heart will be cracked open. Because you’ve searched for meaning and worth outside yourself, you’ll be forced to look within. Who am I? What are my values? Why do I exist? Do I love myself unconditionally? All your healthy and toxic patterns are rooted in these questions. Nonjudgmental self-curiosity is your friend. Excavate your subconscious. It’ll be scary and uncomfortable. Your ego will resist. But it’s worth it. You’ll learn that fear is expensive for business. That much of your suffering is self-inflicted and preventable. And that your best leadership comes from love and service. And sometimes, love demands the uncomfortable action you’ve been avoiding - firing someone, saying no to a board member, etc.
All the business stuff - customer acquisition, fundraising, building an executive team, etc - is important. But you’re smart and scrappy. You’ll figure it out. The most impactful (and most challenging) opportunities are within. The highest-return work won’t look like work at all - rest, journaling, community, therapy, meditation, etc. Anything that helps you shift from fear to love. Self-mastery is the ultimate game. Do the inner work.
Lesson 2: Cry More. Seriously.
Heavy is the head that wears the crown. Your decade as CEO will feel terribly lonely. You will carry a lot and hurt in silence. You’ll be world-class at shoving your emotions aside and distracting yourself with work. Unfortunately, emotional debt collects interest. It will fester in your subconscious, manifesting as addiction, insomnia, passive aggressiveness, exhaustion, resentment, and other toxic behaviors.
At your 2019 annual sales kickoff you’ll watch two hundred colleagues crush it with their presentations and workshops. You did very little, and yet all the right things happened. It feels incredible. As you bring the kickoff to a close with a few words, you’ll be overwhelmed with gratitude and pride. You’ll unexpectedly burst into tears in front of everyone. Yikes! How embarrassing! Strong CEOs never cry. You’ve cried maybe five times in your whole life. And yet, multiple colleagues will share that they’re ready to run through walls because of your vulnerability. And it feels good to let it out. What’s going on? Eventually you’ll learn a timeless leadership truth - people follow hearts first. Minds second.
All your life you’ve believed that you have to be perfect and strong. That only weak people show emotions. Fear has conditioned you to guard your heart with toxic positivity. The 5 Dysfunctions of a Team will teach you that teams need trust and healthy conflict to achieve great results. And what builds trust? Vulnerability. Teams that seek and speak truth instead of harmony outperform those that do not. When you own your messiness and name your emotions out loud, it gives others permission to do the same. Your shared humanity builds stronger bonds and encourages more honest conversations. Programs like Leaders in Tech (based on the legendary “Touchy Feely” Stanford GSB class) will help you develop your emotional literacy. You’ll realize how in your head you’ve been, disconnected from your body, where emotions live. You’ll learn how to identify when you’re feeling sad, angry, proud, grateful, and the full richness of human emotions. You’ll learn how to express those emotions in healthier ways and value their intelligence. You’ll see the gap between what you say/do and how you really feel, and how your inauthenticity hurts yourself and others around you. In these moments, your heart already knew what to do - fire someone sooner, say no, ask for help. Your mind was just too preoccupied to listen.
Eventually you’ll learn that there’s nothing braver than asking for help. That the people who love you will show up for you in ways you didn’t believe you deserved. Just talking about stuff helps. As you share your deepest darkest secrets and cry more, it gives others permission to do the same. Turns out you’re not the only one who’s fighting a battle. Suddenly the journey doesn’t feel so lonely.
Lesson 3: Surrender.
Your harsh inner critic will drown out your inner cheerleader. Building a billion dollar company won’t make you happy. You’ll meet wildly successful business leaders with all the money, power, and status. And yet, they are miserable. Joyless. Friendless. Addicted. Unkind. You used to crave what they have but now it doesn’t seem so appealing. Deep down, a tender, knowing voice whispers. Something needs to change. Maybe it’s time to redefine success. You’ll wonder if it’s time to step down as CEO after sprinting for a decade and hitting a wall. But your stubborn ego will be too scared and proud to let go. And it certainly doesn’t like big change. Your company, your role, and your identity are now one and the same. People won’t like me if I’m not a CEO.
Sitting with ayahuasca in the darkness of the Mexican jungle will give you the tough love you need. It will be the most challenging experience of your life, ten times more so than building a company. This is the deepest darkest stuff that you’ve been avoiding your whole life. The deepest, darkest emotions you've avoided your whole life: resentment, anger, sadness, shame, and guilt. It’s time for your ego to die. The caterpillar must enter the void so that the butterfly can emerge. But your ego is white-knuckling and not letting go.
The plant medicine is wise and powerful beyond comprehension. She may be tough, but she always wants the best for you. She holds up a fierce yet compassionate mirror of truth that you cannot lie to. After much reflection, the medicine helps you realize that business is just a game. Your self-worth is not tied to your job title, company valuation, or employee count. The medicine shows you how much you people-please. You never needed approval from others. It’s okay to say no and be disliked and rejected.
Stop trading your truth for false harmony. Clear is kind. And kindness is king.
You’ll realize that you’ve always done your best, even when it didn’t feel like it. And so is everyone else. If you could have done better or differently, you would have. Giving yourself and others more grace does not lower your standards. With more reflection and medicine, the master lesson reveals itself.
Everything you needed was already within you. You didn’t have to achieve, perform, please, or prove. You were, are, and will always be a human being, not a human doing.
You belong. You are worthy.
Wow!!
Love this